126764-17-8

Basic information

• Product Name: 1-Chloro-6,6-dimethyl-5-hept-2-en-4-ino
• Synonyms: 1-Chloro-6,6-dimethylhept-2-en-4-yne(cis+trans);1-chloro-6,6-dimethyl-5-hept-2-en-4-yne;1-CHLORO-6,6-DIMETHYL-2-ENE-4-YNE-HEPTANE;1-CHLORO-6,6-DIMETHYL-2-HEPTEN-4-YNE;2-HEPTEN-4-YNE, 1-CHLORO-6,6-DIMETHYL-, (2E)-;TRANS-1-CHLORO-6,6-DIMETHYL-2-HEPTENE-4-YNE;1-chloro-6,6-dimethyl-2-ene-4-yene-heptane;1-chloro-6,6-dimethyl-2-hepten-4-yn
• CAS NO: 126764-17-8
• Molecular Formula: C9H13Cl
• Molecular Weight: 156.65
• EINECS: 1806241-263-5
• Product Categories: (intermediate of terbinafine hcl);Miscellaneous Reagents;API Intermediate
• Mol File: 126764-17-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 207-208°C
• Flash Point: 75°C
• Appearance: /
• Density: 0.946
• Vapor Pressure: 0.324mmHg at 25°C
• Refractive Index: 1.4850
• Storage Temp.: Amber Vial, Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform, Ethyl Acetate (Slightly), Hexane (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 1-Chloro-6,6-dimethyl-5-hept-2-en-4-ino(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-6,6-dimethyl-5-hept-2-en-4-ino(126764-17-8)
• EPA Substance Registry System: 1-Chloro-6,6-dimethyl-5-hept-2-en-4-ino(126764-17-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• Hazardous Substances Data: 126764-17-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

An intermediate in the synthesis of Terbinafine (T107500).

InChI:InChI=1/C9H13Cl/c1-9(2,3)7-5-4-6-8-10/h4,6H,8H2,1-3H3/b6-4+

Synthetic route

3-hydroxy-6,6-dimethylhept-1-ene-4-yne (78629-20-6) → 1-chloro-6,6-dimethyl-2-hepten-4-yne (126764-17-8)

Conditions	Yield
With hydrogenchloride; trichlorophosphate In water; acetonitrile at 10 - 28℃; for 6.33333h;
With hydrogenchloride In water; acetonitrile at 0 - 20℃; for 9h;

1-chloro-6,6-dimethyl-2-hepten-4-yne (126764-17-8) + N-methyl-1-naphthalenemethylamine hydrochloride (65473-13-4) → terbinafine hydrochloride (78628-80-5)

Conditions	Yield
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine hydrochloride With sodium carbonate In water; N,N-dimethyl-formamide at 11 - 60℃; for 6.25h; Stage #2: With hydrogenchloride In water for 0.5h; pH=0.2;
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine hydrochloride With sodium carbonate In water; N,N-dimethyl-formamide at 10 - 75℃; for 6.75h; Stage #2: With hydrogenchloride In dichloromethane; water at 10 - 15℃; for 0.5h; Product distribution / selectivity;
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine hydrochloride With sodium carbonate In water at 10 - 75℃; for 6.75h; Stage #2: With hydrogenchloride In dichloromethane; water at 10 - 15℃; for 0.5h; Product distribution / selectivity;

1-chloro-6,6-dimethyl-2-hepten-4-yne (126764-17-8) + N-methyl-1-naphthalenemethylamine (14489-75-9) → terbinafine hydrochloride (78628-80-5)

Conditions	Yield
Stage #1: 1-chloro-6,6-dimethyl-2-hepten-4-yne; N-methyl-1-naphthalenemethylamine With sodium hydroxide In water at 20 - 100℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 1h;

1-chloro-6,6-dimethyl-2-hepten-4-yne (126764-17-8) + N-methyl-1-naphthalenemethylamine hydrochloride (65473-13-4) → terbinafin (91161-71-6)

Conditions	Yield
With sodium carbonate In water at 10 - 75℃; for 6.75h; Product distribution / selectivity;
With sodium carbonate In water; N,N-dimethyl-formamide at 10 - 75℃; for 6.75h; Product distribution / selectivity;

1-chloro-6,6-dimethyl-2-hepten-4-yne (126764-17-8) + 5-methyl-indole-2,3-dione (608-05-9) → 1-[(R)-4,4-dimethyl-1-vinyl-2-pentynyl]-5-methyl-2,3-indolinedione + 1-[(S)-4,4-dimethyl-1-vinyl-2-pentynyl]-5-methyl-2,3-indolinedione

Conditions	Yield
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; benzyl ((11bS)-2,6-bis(3,5-di(tert-butyl)-4-methoxyphenyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphosphepin-4-yl)-L-prolinate; N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester at 40℃; Sealed tube; Overall yield = 40 percent; Overall yield = 56 mg; enantioselective reaction;	A n/a B n/a

Upstream product

• 78629-20-6 3-hydroxy-6,6-dimethylhept-1-ene-4-yne 

Downstream Products

• 78628-80-5 terbinafine hydrochloride 
• 91161-71-6 terbinafin 

Relevant articles and documents

PROCESS FOR PREPARING TERBINAFINE

A process for preparing terbinafine or a salt thereof having high purity.